US4551493A - Transparent flame-retardant poly(arylether-arylsulfone) molding materials - Google Patents

Transparent flame-retardant poly(arylether-arylsulfone) molding materials Download PDF

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US4551493A
US4551493A US06/581,715 US58171584A US4551493A US 4551493 A US4551493 A US 4551493A US 58171584 A US58171584 A US 58171584A US 4551493 A US4551493 A US 4551493A
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poly
arylether
arylsulfone
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Gerd Blinne
Volker Muench
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BASF SE
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/34—Heterocyclic compounds having nitrogen in the ring
    • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
    • C08K5/3432—Six-membered rings
    • C08K5/3437—Six-membered rings condensed with carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/18—Amines; Quaternary ammonium compounds with aromatically bound amino groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L81/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur with or without nitrogen, oxygen or carbon only; Compositions of polysulfones; Compositions of derivatives of such polymers
    • C08L81/06—Polysulfones; Polyethersulfones

Definitions

  • Aromatic polysulfones form the subject of a large number of publications, patents and patent applications. Examples of such publications include J. Chem. Soc. (1961), 1604-1610, J. Polym. Sci. 40 (1959), 399-406, GB-A No. 1 078 234, GB-A No. 1 016 245 and GB-A No. 1 060 546.
  • the present invention hence relates to transparent flame-retardant poly(arylether-arylsulfone) molding materials which contain a poly(2,6-dibromophenylene 1,4-oxide) as a flameproofing agent.
  • Poly(2,6-dibromophenylene 1,4-oxides) which can be used in accordance with the invention have molecular weights of from 1000 to 20,000, preferably from 2000 to 6000, and are prepared by polycondensation of 2,4,6-tribromophenol in the presence of an alkali metal hydroxide, e.g. sodium hydroxide, by a conventional process, for example as described in DE-A No. 2 948 263, or DE-A No. 3 002 658 or by S. Yoshida and H. Kawahara in American Chemical Society, Division of Polymer Chemistry, Polymer Preprints, Volume 20, part 1 (1979), pages 861-862 or J. F. Harrod, P. van Gheluwe, D. Kisakurek and A. Shaver in Macromolecules, volume 14 (1981), pages 565-570.
  • an alkali metal hydroxide e.g. sodium hydroxide
  • the poly(2,6-dibromophenylene 1,4-oxides) are used in amounts of from 0.1 to 10.0, preferably from 0.5 to 3.0, % by weight, based on the weight of the poly(arylether-arylsulfones). In the case of pure poly(arylether-arylsulfones), from 0.1 to 3.0% by weight of the novel flameproofing agent has proven particularly useful.
  • a conventional heat stabilizer in addition to the poly(2,6-dibromophenylene 1,4-oxide), from 0.1 to 5.0, preferably from 0.3 to 3, % by weight, based on the weight of the poly(arylether-arylsulfone), of a conventional heat stabilizer is incorporated into the transparent flame-retardant poly(arylether-arylsulfone) molding material.
  • Preferred heat stabilizers are sterically hindered phenols, as marketed, for example, under the Ciba Geigy trademark ® Irganox, and in particular cyclic and/or or linear diphenylamine/acetone condensates having molecular weights of from 227 to 624.
  • Suitable diphenylamine/acetone condensates can be prepared by condensation of diphenylamine and acetone in a molar ratio of from 1:1 to 2:1, preferably from 1:1 to 1.5:1 by conventional methods described in, for example, U.S. Pat. Nos. 1,906,935, 1,975,167 and 2,002,642.
  • the diphenylamine can be employed together with aromatics which are unsubstituted or substituted, for example by linear or branched alkyl groups of 1 to 4 carbon atoms, the molar ratio of diphenylamine to aromatics being from 1:2 to 2:1, preferably 1:2.
  • aromatics which are unsubstituted or substituted, for example by linear or branched alkyl groups of 1 to 4 carbon atoms, the molar ratio of diphenylamine to aromatics being from 1:2 to 2:1, preferably 1:2.
  • Examples include ethyl benzene, n-propyl benzene, isopropyl benzene, n-butyl benzene, sec.-butyl benzene and preferably toluene and benzene, as well as mixtures of aromatics.
  • Suitable cyclic or linear diphenylamine/acetone condensates are compounds of the general formulae ##STR3## where the radicals R are identical or different and are each preferably alkyl of 1 to 4 carbon atoms and in particular methyl and/or hydrogen. Compounds which have proven particularly useful and are therefore preferably used are ##STR4##
  • the sterically hindered phenols and the cyclic or linear diphenylamine/acetone condensates having molecular weights of from 227 to 624 can be employed individually or as mixtures, including industrial mixtures.
  • Poly(arylether-arylsulfone) molding materials which have proven to be particularly useful and are therefore preferably used are those which contain from 0.1 to 10, preferably from 0.1 to 3, % by weight of a poly(2,6-dibromophenylene 1,4-oxide) and from 0.1 to 5, preferably from 0.3 to 3.0, % by weight of ##STR5## the percentages being based on the weight of the poly(arylether-arylsulfone).
  • poly(2,6-dibromophenylene 1,4-oxides) which can be employed according to the invention are useful for flameproofing aromatic polysulfones which contain repeating units of the formula
  • the transparent flame-retardant molding materials are prepared using, in particular, poly(arylether-arylsulfones) which essentially consist of units of the formula ##STR6## Where n is an integer from 30 to 100, preferably from 40 to 80.
  • aromatic polysulfones have also proven useful, so that compounds of this type which consist of not less than 50% by weight, based on the total weight of the aromatic polysulfones, of units of the formula ##STR7## and furthermore contain condensed units of comonomers are likewise preferred.
  • suitable comonomers give, for example, units of the formula
  • Ar 1 and Ar 2 are each an unsubstituted or substituted aromatic radical which may be identical or different
  • Y is --SO 2 --, --S--, --S--S--, --CO--, C 1 -C 12 -alkylene, C 2 -C 12 -alkylidene, C 5 -C 12 -cycloalkylene or C 7 -C 12 -arylalkylene
  • m is O or 1 and Z is -O- or -S-.
  • Aromatic polysulfones of this type have molecular weights of from 15,000 to 50,000, preferably from 20,000 to 40,000, and intrinisic viscosities (measured at 20° C. in a 1% strength by weight N-methylpyrrolidone solution) of from 0.35 to 0.85, preferably from 0.40 to 0.70.
  • novel poly(arylether-arylsulfone) molding materials are advantgeously prepared by mixing the molten poly(arylether-arylsulfone) which, as stated above, preferably contains not less than 50% by weight of units of the formula ##STR8## with the poly(2,6-dibromophenylene 1,4-oxide) and, if required, a heat stabilizer, for example with the aid of a kneader, an intensive mixer, a stator-rotor mixer, a roll mill or, preferably, an extruder at from 280° to 380° C., preferably from 300° to 360° C.
  • the pulverulent of granulated poly(arylether-arylsulfones) can be powdered with the flameproofing agent and, where relevant, the heat stabilizer, or can be treated with solutions of these, and the molding material can then be dried.
  • the novel poly(arylether-arylsulfone) molding materials can be mixed with other thermoplastics, e.g. polyesters, nylons, polyurethanes, polyolefines, polyvinyl chloride or polyoxymethylenes, in amounts of from 5 to 50, preferably from 20 to 50, % by weight, based on the poly(arylether-arylsulfone). Furthermore, they can be modified with reinforcing fillers, transparent or opaque pigments and other assistants and additives.
  • other thermoplastics e.g. polyesters, nylons, polyurethanes, polyolefines, polyvinyl chloride or polyoxymethylenes
  • reinforcing fillers are asbestos, coal and preferably glass fibers, the latter being used, for example, in the form of glass fabrics, glass mats, surfacing mats and/or preferably glass rovings or cut glass filaments obtained from low-alkali E glass and having a diameter of from 5 to 20, preferably from 8 to 15 ⁇ m; after incorporation, the glass fibers have a mean length of from 0.05 to 1, preferably from 0.1 to 0.5, mm.
  • the poly(arylether-arylsulfone) molding materials reinforced with glass rovings or cut glass filaments contain from 10 to 60, preferably from 20 to 50, % by weight, based on the total weight, of the reinforcing agent, while the impregnated glass fabrics, glass mats and/or surfacing mats contain from 10 to 80, preferably from 30 to 60, % by weight, based on the total weight, of poly(arylether-arylsulfones).
  • suitable pigments are titanium dioxide, cadmium sulfide, zinc sulfide, barium sulfate and carbon black.
  • additives and assistants are dyes, lubricants, e.g.
  • the poly(arylether-arylsulfone) molding materials according to the invention are used for producing shaped articles, films and fiber.
  • the test for flame retardance was carried out as a vertical burning test for classification under the fire classes 94 VE-0, 94 VE-1 or 94 VE-2, in accordance with the methods of the Underwriter's Laboratories (J. Troitzsch, Brand von Kunststoffen, Hanser-Verlag, Kunststoff, Vienna, 1981, pages 397-399.
  • the test samples used were 1/8" bars.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Fireproofing Substances (AREA)

Abstract

Transparent flame-retardant poly(arylether-arylsulfone) molding materials preferably contain not less than 50% by weight of units of the formula ##STR1## and, as a flameproofing agent, from 0.1 to 10% by weight, based on the weight of poly(arylether-arylsulfone), of a poly(2,6-dibromophenylene 1,4-oxide) having a molecular weight of from 1000 to 20000, and, if required, a heat stabilizer.
The molding materials are useful for the production of shaped articles, films and fibers.

Description

Aromatic polysulfones form the subject of a large number of publications, patents and patent applications. Examples of such publications include J. Chem. Soc. (1961), 1604-1610, J. Polym. Sci. 40 (1959), 399-406, GB-A No. 1 078 234, GB-A No. 1 016 245 and GB-A No. 1 060 546.
Poly(arylether-arylsulfones) containing units of the formula ##STR2## are very useful industrially. For many fields of use, however, high thermal stability as well as good flame-retardance is of considerable importance.
A large number of measures for rendering plastics, including, for example, polyarylsulfones, flame-retardant by means of suitable additives have been described. According to DE-A No. 2 903 100 (GB-A No. 2 039 503), the addition of organic sulfonates leads to self-extinguishing poly(arylether-arylsulfones). According to U.S. Pat. No. 4,049,619, flame-retardant poly-(arylether-arylsulfones) can be prepared with the aid of bromoaromatic ethers, e.g. 1,2-bis(2,4,6-tribromophenoxy)ethane, 1,3-bis(2,4,6-tribromophenoxy)propane or 1,2-bis(2,3,4,5,6-pentabromophenoxy)ethane and oxides of antimony, arsenic or bismuth.
The disadvantage of the processes given as examples and of the conventional flame-retardant poly(arylether-arylsulfones) is that the molding materials lose their transparency due to the addition of the flameproofing agents, have a pronounced tendency to decompose and are volatile at the high processing temperatures. The two last-mentioned disadvantageous properties result in poorer flame retardance and undesirable discolorations.
It is an object of the present invention to provide flame-retardant poly(arylether-arylsulfone) molding materials without the good transparency of the unmodified molding materials being adversely affected by the additives.
We have found, surprisingly, that this object is achieved by the use of poly(2,6-dibromophenylene 1,4-oxides) as flameproofing agents, with or without heat stabilizers.
The present invention hence relates to transparent flame-retardant poly(arylether-arylsulfone) molding materials which contain a poly(2,6-dibromophenylene 1,4-oxide) as a flameproofing agent.
Poly(2,6-dibromophenylene 1,4-oxides) which can be used in accordance with the invention have molecular weights of from 1000 to 20,000, preferably from 2000 to 6000, and are prepared by polycondensation of 2,4,6-tribromophenol in the presence of an alkali metal hydroxide, e.g. sodium hydroxide, by a conventional process, for example as described in DE-A No. 2 948 263, or DE-A No. 3 002 658 or by S. Yoshida and H. Kawahara in American Chemical Society, Division of Polymer Chemistry, Polymer Preprints, Volume 20, part 1 (1979), pages 861-862 or J. F. Harrod, P. van Gheluwe, D. Kisakurek and A. Shaver in Macromolecules, volume 14 (1981), pages 565-570.
Depending on the poly(arylether-arylsulfones) and on the additives and assistants which may be present in the molding materials, the poly(2,6-dibromophenylene 1,4-oxides) are used in amounts of from 0.1 to 10.0, preferably from 0.5 to 3.0, % by weight, based on the weight of the poly(arylether-arylsulfones). In the case of pure poly(arylether-arylsulfones), from 0.1 to 3.0% by weight of the novel flameproofing agent has proven particularly useful.
In a preferred embodiment, in addition to the poly(2,6-dibromophenylene 1,4-oxide), from 0.1 to 5.0, preferably from 0.3 to 3, % by weight, based on the weight of the poly(arylether-arylsulfone), of a conventional heat stabilizer is incorporated into the transparent flame-retardant poly(arylether-arylsulfone) molding material.
Preferred heat stabilizers are sterically hindered phenols, as marketed, for example, under the Ciba Geigy trademark ® Irganox, and in particular cyclic and/or or linear diphenylamine/acetone condensates having molecular weights of from 227 to 624.
Suitable diphenylamine/acetone condensates can be prepared by condensation of diphenylamine and acetone in a molar ratio of from 1:1 to 2:1, preferably from 1:1 to 1.5:1 by conventional methods described in, for example, U.S. Pat. Nos. 1,906,935, 1,975,167 and 2,002,642.
For the condensation with acetone, the diphenylamine can be employed together with aromatics which are unsubstituted or substituted, for example by linear or branched alkyl groups of 1 to 4 carbon atoms, the molar ratio of diphenylamine to aromatics being from 1:2 to 2:1, preferably 1:2. Examples include ethyl benzene, n-propyl benzene, isopropyl benzene, n-butyl benzene, sec.-butyl benzene and preferably toluene and benzene, as well as mixtures of aromatics.
Examples of suitable cyclic or linear diphenylamine/acetone condensates are compounds of the general formulae ##STR3## where the radicals R are identical or different and are each preferably alkyl of 1 to 4 carbon atoms and in particular methyl and/or hydrogen. Compounds which have proven particularly useful and are therefore preferably used are ##STR4##
The sterically hindered phenols and the cyclic or linear diphenylamine/acetone condensates having molecular weights of from 227 to 624 can be employed individually or as mixtures, including industrial mixtures.
Poly(arylether-arylsulfone) molding materials which have proven to be particularly useful and are therefore preferably used are those which contain from 0.1 to 10, preferably from 0.1 to 3, % by weight of a poly(2,6-dibromophenylene 1,4-oxide) and from 0.1 to 5, preferably from 0.3 to 3.0, % by weight of ##STR5## the percentages being based on the weight of the poly(arylether-arylsulfone).
The amounts of novel flameproofing agent and heat stabilizer incorporated have virtually no adverse effect on the transparency of the molding materials.
The poly(2,6-dibromophenylene 1,4-oxides) which can be employed according to the invention are useful for flameproofing aromatic polysulfones which contain repeating units of the formula
--Ar--SO.sub.2 --
Where Ar is a divalent aromatic radical. The transparent flame-retardant molding materials are prepared using, in particular, poly(arylether-arylsulfones) which essentially consist of units of the formula ##STR6## Where n is an integer from 30 to 100, preferably from 40 to 80. However, owing to the great variability in the mechanical properties, aromatic polysulfones have also proven useful, so that compounds of this type which consist of not less than 50% by weight, based on the total weight of the aromatic polysulfones, of units of the formula ##STR7## and furthermore contain condensed units of comonomers are likewise preferred. When condensed, suitable comonomers give, for example, units of the formula
--Ar.sup.1 --(Y).sub.m --Ar.sup.2 --Z
where Ar1 and Ar2 are each an unsubstituted or substituted aromatic radical which may be identical or different, Y is --SO2 --, --S--, --S--S--, --CO--, C1 -C12 -alkylene, C2 -C12 -alkylidene, C5 -C12 -cycloalkylene or C7 -C12 -arylalkylene, m is O or 1 and Z is -O- or -S-.
Aromatic polysulfones of this type have molecular weights of from 15,000 to 50,000, preferably from 20,000 to 40,000, and intrinisic viscosities (measured at 20° C. in a 1% strength by weight N-methylpyrrolidone solution) of from 0.35 to 0.85, preferably from 0.40 to 0.70.
The novel poly(arylether-arylsulfone) molding materials are advantgeously prepared by mixing the molten poly(arylether-arylsulfone) which, as stated above, preferably contains not less than 50% by weight of units of the formula ##STR8## with the poly(2,6-dibromophenylene 1,4-oxide) and, if required, a heat stabilizer, for example with the aid of a kneader, an intensive mixer, a stator-rotor mixer, a roll mill or, preferably, an extruder at from 280° to 380° C., preferably from 300° to 360° C. In another version of the process, the pulverulent of granulated poly(arylether-arylsulfones) can be powdered with the flameproofing agent and, where relevant, the heat stabilizer, or can be treated with solutions of these, and the molding material can then be dried.
If transparency is only of minor importance with regard to the use of the materials, or is not required, the novel poly(arylether-arylsulfone) molding materials can be mixed with other thermoplastics, e.g. polyesters, nylons, polyurethanes, polyolefines, polyvinyl chloride or polyoxymethylenes, in amounts of from 5 to 50, preferably from 20 to 50, % by weight, based on the poly(arylether-arylsulfone). Furthermore, they can be modified with reinforcing fillers, transparent or opaque pigments and other assistants and additives.
Examples of reinforcing fillers are asbestos, coal and preferably glass fibers, the latter being used, for example, in the form of glass fabrics, glass mats, surfacing mats and/or preferably glass rovings or cut glass filaments obtained from low-alkali E glass and having a diameter of from 5 to 20, preferably from 8 to 15 μm; after incorporation, the glass fibers have a mean length of from 0.05 to 1, preferably from 0.1 to 0.5, mm. The poly(arylether-arylsulfone) molding materials reinforced with glass rovings or cut glass filaments contain from 10 to 60, preferably from 20 to 50, % by weight, based on the total weight, of the reinforcing agent, while the impregnated glass fabrics, glass mats and/or surfacing mats contain from 10 to 80, preferably from 30 to 60, % by weight, based on the total weight, of poly(arylether-arylsulfones). Examples of suitable pigments are titanium dioxide, cadmium sulfide, zinc sulfide, barium sulfate and carbon black. Examples of other additives and assistants are dyes, lubricants, e.g. graphite or molybdenum disulfide, abrasives, e.g. carborundum, light stabilizers and hydrolysis retardants. The pigments, additives and assistants are conventionally employed in amounts of from 0.01 to 3% by weight, based on the weight of poly(arylether-arylsulfone).
The poly(arylether-arylsulfone) molding materials according to the invention are used for producing shaped articles, films and fiber.
The Examples and Comparative Examples which follow illustrate the invention. Parts and percentages are by weight. The test for flame retardance was carried out as a vertical burning test for classification under the fire classes 94 VE-0, 94 VE-1 or 94 VE-2, in accordance with the methods of the Underwriter's Laboratories (J. Troitzsch, Brandverhalten von Kunststoffen, Hanser-Verlag, Munich, Vienna, 1981, pages 397-399. The test samples used were 1/8" bars.
EXAMPLES AND COMPARATIVE EXAMPLES General method
The flameproofing agents and, where relevant, heat stabilizers shown in the Table below, together with a poly(arylether-arylsulfone) which essentially consisted of repeating units of the formula ##STR9## (®Udel P-1700 from Union Carbide Corp.), were melted and homogenized at 330° C. in an extruder, and then granulated. Using an injection molding technique, the granules were converted at 330° C. to test samples, and these were used to determine the transparency, the color and the flammability rating.
In the Table, the heat stabilizers are indicated as follows:
__________________________________________________________________________
 ##STR10##                                                                
(® Naugard 445 from Uniroyal)                                         
1010: sterically hindered phenol                                          
(® Irganox 1010 from Ciba Geigy).                                     
                      Heat sta-                                           
       Flameproofing agent                                                
                      bilizer                                             
                 Amount  Amount     Trans-                                
                                          UL*-                            
       Type      [%]  Type                                                
                         [%]  Color parency                               
                                          94 Test                         
__________________________________________________________________________
Example                                                                   
1      Poly(2,6-dibromo-                                                  
                 0.2  -- --   Very pale                                   
                                    Very good                             
                                          VE-1                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
2      Poly(2,6-dibromo-                                                  
                 0.5  -- --   Very pale                                   
                                    Very good                             
                                          VE-1                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
3      Poly(2,6-dibromo-                                                  
                 1.0  -- --   Pale  Very good                             
                                          VE-0                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
4      Poly(2,6-dibromo-                                                  
                 3.0  -- --   Pale  Very good                             
                                          VE-0                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
5      Poly(2,6-dibromo-                                                  
                 0.5   445                                                
                         0.5  Pale  Very good                             
                                          VE-0                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
6      Poly(2,6-dibromo-                                                  
                 0.5  1010                                                
                         0.5  Very pale                                   
                                    Very good                             
                                          VE-0                            
       phenylene 1,4-                                                     
       oxide)                                                             
       (molecular weight                                                  
       5000)                                                              
Comparative                                                               
Examples                                                                  
1      --        --   -- --   Very pale                                   
                                    Very good                             
                                          VE-2                            
2      SO.sub.3 Na                                                        
                 1.0  -- --   Beige Opaque                                
                                          VE-0                            
3      Antimony trioxide                                                  
                 3.0  -- --   Beige Opaque                                
                                          VE-0                            
4      Decabromodiphenyl                                                  
                 3.0  -- --   Brown Good  VE-2                            
       ether                                                              
__________________________________________________________________________
 *Underwriter's Laboratories
The Examples and Comparative Examples showed that only poly(arylether-arylsulfone) molding materials which contained, as flameproofing agents, the novel poly(2,6-dibromophenylene 1,4-oxides) having a molecular weight of about 2000 to 6000 were flame-retardant and at the same time transparent, and had a pale color.

Claims (8)

We claim:
1. A transparent, flame-retardant molding composition which comprises:
poly(arylether-arylsulfone) molding material, and
an effective amount of a poly(2,6-dibromophenylene 1,4-oxide) as a flameproofing agent.
2. A transparent flame-retardant poly(arylether-arylsulfone) molding material as set forth in claim 1, wherein the poly(2,6-dibromophenylene 1,4-oxide) has a molecular weight of from 1000 to 20,000.
3. A transparent flame-retardant poly(arylether-arylsulfone) molding material as set forth in claim 1, which contains the poly(2,6-dibromophenylene 1,4-oxide) in an amount of from 0.1 to 10.0% by weight, based on the weight of poly(arylether-arylsulfone).
4. The molding material of claim 1, which further contains a heat stabilizer.
5. The molding material of claim 1, which contains a poly(2,6-dibromophenylene 1,4-oxide) and, in addition, from 0.1 to 5.0% by weight, based on the weight of poly(arylether-arylsulfone), of a heat stabilizer from the group consisting of cyclic and/or linear diphenylamine/acetone condensates.
6. A transparent flame-retardant poly(arylether-arylsulfone) molding material as set forth in claim 1, which contains
from 0.1 to 10.0% by weight of a poly(2,6-dibromophenylene 1,4-oxide) and
from 0.1 to 5.0% by weight of ##STR11## the percentages being based on the weight of the poly(arylether-arylsulfone).
7. A transparnt flame-retardant poly(arylether-arylsulfone) molding material as set forth in claim 1, wherein the poly(arylether-arylsulfone) contains not less than 50% by weight of units of the formula ##STR12##
8. A transparent flame-retardant poly(arylether-arylsulfone) molding material as set forth in claim 1, wherein the poly(arylether-arylsulfone) essentially consists of units of the formula ##STR13## where n is an integer from 30 to 100.
US06/581,715 1983-03-01 1984-02-21 Transparent flame-retardant poly(arylether-arylsulfone) molding materials Expired - Fee Related US4551493A (en)

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US4873278A (en) * 1986-11-14 1989-10-10 General Electric Company Inhibition of irradiation yellowing in polysulfone compositions
US4929497A (en) * 1989-03-27 1990-05-29 Albany International Corp. Flame retardant rolling door
US20030035917A1 (en) * 1999-06-11 2003-02-20 Sydney Hyman Image making medium
US8669325B1 (en) 1999-06-11 2014-03-11 Sydney Hyman Compositions image making mediums and images
US8921473B1 (en) 2004-04-30 2014-12-30 Sydney Hyman Image making medium
US9744800B2 (en) 1999-06-11 2017-08-29 Sydney Hyman Compositions and image making mediums
US9786194B2 (en) 1999-06-11 2017-10-10 Sydney Hyman Image making medium compositions and images
US11355027B2 (en) 2004-04-30 2022-06-07 Sydney Hyman Image making medium compositions and images

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ATE405946T1 (en) 2005-06-10 2008-09-15 Soitec Silicon On Insulator CALIBRATION METHOD FOR THERMAL TREATMENT APPARATUS

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US3830766A (en) * 1970-09-23 1974-08-20 Kalk Chemische Fabrik Gmbh Self-extinguishing moulding composition
US3989531A (en) * 1971-08-05 1976-11-02 General Electric Company Fire-retardant polymeric compositions containing brominated biphenols
US4038248A (en) * 1973-02-08 1977-07-26 Velsicol Chemical Corporation Plastic compositions
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* Cited by examiner, † Cited by third party
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US4873278A (en) * 1986-11-14 1989-10-10 General Electric Company Inhibition of irradiation yellowing in polysulfone compositions
US4929497A (en) * 1989-03-27 1990-05-29 Albany International Corp. Flame retardant rolling door
US20030035917A1 (en) * 1999-06-11 2003-02-20 Sydney Hyman Image making medium
US7629400B2 (en) 1999-06-11 2009-12-08 Sydney Hyman Image making medium
US8669325B1 (en) 1999-06-11 2014-03-11 Sydney Hyman Compositions image making mediums and images
US9744800B2 (en) 1999-06-11 2017-08-29 Sydney Hyman Compositions and image making mediums
US9786194B2 (en) 1999-06-11 2017-10-10 Sydney Hyman Image making medium compositions and images
US11341863B2 (en) 1999-06-11 2022-05-24 Sydney Hyman Compositions and image making media
US8921473B1 (en) 2004-04-30 2014-12-30 Sydney Hyman Image making medium
US11355027B2 (en) 2004-04-30 2022-06-07 Sydney Hyman Image making medium compositions and images

Also Published As

Publication number Publication date
EP0120296B1 (en) 1986-06-04
DE3307051A1 (en) 1984-09-06
EP0120296A1 (en) 1984-10-03
DE3460191D1 (en) 1986-07-10

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